Hedge fund manager Steven Cohen recently purchased “Le Rêve,” a 1932 oil painting of Picasso’s mistress, from casino mogul Steve Wynn for an astounding $155 million. According to the New York Post, this is the highest amount that a U.S. collector has ever paid for a piece of artwork.

Though the price may seem staggering for even the most serious art collectors, Cohen and Wynn both have a history with this particular Picasso painting. In 2006, Wynn accidentally put his elbow through the canvas of “Le Rêve” while showing it to several friends — including Nora Ephron — only one day after he agreed to sell it to Cohen for $139 million. The incident created a six-inch tear that was later repaired for $90,000. “It’s superbly restored,” Beverly Schreiber Jacoby, President of New York-based BSJ Fine Art, told Bloomberg News. “If you didn’t know that it has been damaged, you would not see it.”

Both Cohen and Wynn are well-known art collectors. Cohen’s collection is reportedly worth $1 billion and includes major works by De Kooning, Jasper Johns, Bacon, Koons, Van Gogh and Manet. He is also the owner of Damien Hirst’s formaldehyde shark and “The Physical Impossibility of Death in the Mind of Someone Living.”